The phenolic hydroxyl group-containing resin has been widely used in electrical and electronic fields such as a semiconductor sealing material or a printed circuit board insulating material, as a curable resin composition which has the phenolic hydroxyl group-containing resin per se as the main agent or a curing agent for as an epoxy resin, etc., from the viewpoint of the fact that a cured product obtained therefrom has excellent heat resistance and moisture resistance, in addition to being used for adhesives, molding materials, paint, photoresist materials, epoxy resin raw materials, or curing agents for epoxy resins.
Among these, in the field of semiconductor resist materials, a cresol novolac resin is preferably utilized (refer to PTL 1) since a cured product obtained therefrom exhibits high heat resistance. However, the conventional novolac resin obtained by reaction of cresol with formalin in the presence of an acid catalyst, described in PTL 1 has excellent heat resistance, but does not have sufficient alkali developing properties.
In addition, from the viewpoint of the fact that a compound having a cylindrical structure called a calixarene structure has a high glass transition temperature or a high melting point, and excellent heat stability, applications to various electric and electronic materials are expected. For example, a 1-naphthol type calix [4] arene compound obtained by reacting 1-naphthol and formaldehyde in a proportion in which the molar ratio [1-naphthol/formaldehyde] becomes equal to or less than 1.0 under basic catalyst conditions such as sodium hydroxide is known (refer to PTL 2). However, the 1-naphthol type calix (4) arene compound described in PTL 2 does not have sufficient solubility in general-purpose organic solvents, and thus, applications to adhesives or paints, photoresists, printed circuit boards are difficult.